Piperidine → HCID 66546510, compound

HRID 1853099Notes

Reaction equation

HRID 1853099 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]([C:17]3[C:18](=[O:30])[N:19]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[N:20]([CH3:23])[C:21]=3[CH3:22])=[O:16])=[CH:10][CH:9]=2)[C:5](/[N:31]=C/N(C)C)=[N:4][CH:3]=1.[NH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1>CS(C)=O.CC#N.C([O-])([O-])=O.[K+].[K+]>[NH2:31][C:5]1[C:6]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][C:15]([C:17]3[C:18](=[O:30])[N:19]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[N:20]([CH3:23])[C:21]=3[CH3:22])=[O:16])=[CH:12][CH:13]=2)=[N:7][C:2]([N:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)=[CH:3][N:4]=1

Participants

6

Reactant 2

HCID 8082PiperidineHCID 178429251HCID 178429251, compound

Product 1

HCID 66546510HCID 66546510, compoundYield 586.9%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 6342AcetonitrileSolventHCID 11430Potassium CarbonateSolvent

Conditions

Temperature
120 °C

Procedure

The compound prepared in Example 36 (80 mg) and piperidine (0.300 mg) were mixed in DMSO (0.400 mL) and heated to 120° C. for 18 hours. The reaction mixture was then diluted with MeCN (10 mL) and aqueous 1M K2CO3 (7 mL) and heated to 155° C. for 17 minutes in the microwave. The organic products were extracted with EtOAc/CH2Cl2 (9:1) and washed with brine. The material was purified by HPLC (H2O/MeCN with 0.1% TFA). The solvent was removed and the residue was dissolved in CH2Cl2 and the residual TFA was removed by PL-HCO3 MP SPE ion exchange column to give the title compound (10 mg) having the following physical data.

Workup

  1. temperatureheated to 155° C. for 17 minutes in the microwave
  2. extractionThe organic products were extracted with EtOAc/CH2Cl2 (9:1)
  3. washwashed with brine
  4. customThe material was purified by HPLC (H2O/MeCN with 0.1% TFA)
  5. customThe solvent was removed
  6. dissolutionthe residue was dissolved in CH2Cl2
  7. customthe residual TFA was removed by PL-HCO3 MP SPE ion exchange column

Sources & evidence

ORD record
ord-56c8c016583a43e6bccdc61f0179f36a
Source dataset
uspto-grants-2015_02
Patent number
US08962623B2

Reaction notes

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